Recently, the organic synthesis reaction using a transition metal complex as a catalyst has been intensively developed, and especially, the asymmetric synthesis using an optically active bidentate phosphine ligand has been enthusiastically studied as a method of efficiently obtaining desired optically active substances. For instance, some reports disclose the development of the asymmetric catalyst using palladium as a transition metal, and there are known Pd(BINAP).sub.2 having the structure (A), (B) (Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T. Organometallics, 1993, 12, 4188), shown below, etc.; however, the palladium complex having the optically active bidentate phosphine as a ligand and coordinating with an water molecule or a hydroxyl group has not been known. ##STR3##
The catalytic asymmetric aldol reaction yielding an optically active .beta.-hydroxyketone is the condensation reaction of silyl enol ether, ketene silylacetal or ketene silylthioacetal and an aldehyde with an optically active Lewis acid catalyst. The examples are described in the literatures such as (a) Heathcock, C. H., In Asymmetric Synthesis; Morison, J. D., Ed.; Academic press: New York:, 1984; Vol. 3, Chapter 2, (b) Heathcock, C. H., In Comprehensive Organic Synthesis; Perganon Press: Oxford, 1991; Vol. 2, Chapter 1.5-1.9, and the like. In the aldol reaction with these asymmetric Lewis acid catalysts, although extremely high asymmetric yields are reported, in view of the nature of the Lewis acid, the catalyst is expected to have an affinity for various oxygen-functional groups and the like in the preparation of medicines, and therefore, the application of such a reaction to complicated compounds is expected to have difficulty.
On the other hand, although the literatures such as Reetz, M. T.; Vougioukas, A. E., Tetrahedron Lett., 1987, 28, 793; Roos, G. H. P.; Haines, R. J.; Raab, C. E., Synth. Commun., 1993, 23, 1251, and the like disclose the catalytic asymmetric aldol reaction via a transition metal enolate which is not expected to have an affinity for various oxygen-functionnal groups and the like, yet the asymmetric yields are not much more than 20%, and hence the development of the transition metal complex having a novel optically active ligand and the efficient asymmetric synthesis using the complex has been desired. Since the asymmetric aldol reaction is applicable to the asymmetric synthesis of the aglycon of polyoxomacrolides such as erythromycin A, erythromycin B and the like, stereochemistry in the aldol reaction has been enthusiastically studied. The compound having a .beta.-hydroxyketone as a moiety is exemplified by gingerol analogues. The gingerols are known as a compound which has cardiotonic activity (Japanese Patent Application Laid-open No. Sho 64-921 and Japanese Patent Application Laid-open No. Hei 6-40895), activity for platelet-aggregation (Japanese Patent Application Laid-open No. Sho 63-72625), analgesic activity (Japanese Patent Application No. Sho 59-1684), anti-inflammatory activity (Japanese Patent Application Laid-open No. Hei 3-90021), anti-parasitic activity (Japanese Patent Application Laid-open No. Hei 2-4711), and the like. Moreover, the mevalonic acid moiety of HMG-CoA reductase inhibitors has a .beta.-hydroxyester, and therefore, a method of efficiently obtaining an optically active .beta.-hydroxyketone is useful. However, the aldol reaction does not proceed and the .beta.-hydroxyketone is not obtained even if the known complex of (A) or (B) is used.